$24 Cheap flight deals from Chicago (CHI) to Casselberry (ORL)

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This Weekend's Flight Deals from Chicago to Casselberry

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Nov 22 - Sun, Nov 23
MDW
Midway Intl.
MCO
Orlando Intl.
$131 Roundtrip, found 4 days ago
$131
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Nov 22 from Midway Intl. to Orlando Intl., returning Sun, Nov 23, priced at $131 found 4 days ago
Sun, Nov 23 - Thu, Nov 27
ORD
O'Hare Intl.
MCO
Orlando Intl.
$162 Roundtrip, just found
$162
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Nov 23 from O'Hare Intl. to Orlando Intl., returning Thu, Nov 27, priced at $162 just found
Fri, Nov 21 - Mon, Nov 24
RFD
Greater Rockford
MCO
Orlando Intl.
$385 Roundtrip, found 3 days ago
$385
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Nov 21 from Greater Rockford to Orlando Intl., returning Mon, Nov 24, priced at $385 found 3 days ago

Airfares from $24 One Way, $58 Round Trip from Chicago to Casselberry

Prices starting at $58 for return flights and $24 for one-way flights to Casselberry were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Feb 13 - Fri, Feb 20
MDW
Chicago
MCO
Orlando
$58 Roundtrip, found 1 hour ago
$58
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Feb 13 from Chicago to Orlando, returning Fri, Feb 20, priced at $58 found 1 hour ago
Fri, Jan 23 - Mon, Jan 26
ORD
Chicago
MCO
Orlando
$68 Roundtrip, found 1 hour ago
$68
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Jan 23 from Chicago to Orlando, returning Mon, Jan 26, priced at $68 found 1 hour ago
Sun, Jan 25 - Fri, Jan 30
ORD
Chicago
MCO
Orlando
$84 Roundtrip, just found
$84
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Jan 25 from Chicago to Orlando, returning Fri, Jan 30, priced at $84 just found
Wed, Feb 18 - Wed, Feb 25
ORD
Chicago
MCO
Orlando
$137 Roundtrip, just found
$137
Roundtrip
just found
Select United flight, departing Wed, Feb 18 from Chicago to Orlando, returning Wed, Feb 25, priced at $137 just found
Wed, Feb 18 - Wed, Feb 25
ORD
Chicago
MCO
Orlando
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Feb 18 from Chicago to Orlando, returning Wed, Feb 25, priced at $137 just found

Casselberry economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,395 reviews)

Jan 7 - Jan 12

5 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Frontier Airlines • Coach
Price was $611, price is now $274 per person
$274
per person
found 1 day ago
It was ok for the price

Reviewed on Sep 27, 2025

Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8.2/10 Very Good! (5,210 reviews)

Dec 28 - Jan 3

6 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
Price was $1,964, price is now $701 per person
$701
per person
found 1 day ago
I was able to check in at 3:00pm but i had to wait till 4:00 to get my key resulting in a long line just to retrieve my key to my room. The elevator was very slow and needs to be updated. The room was updated with zero rugs but the paint inside the bathroom left much to be desired and the bathroom light came on automatically which was a terrible inconvenience for the other person in the room as they got rudely woken up when i had to use the bathroom in the middle of the night. The ac was loud and kept going on and off and wouldnt stay on and the beds although comfy kept hitting my shin when i got in and out of bed because the mattress didnt fit the bed correctly. The breakfast was ok but no fresh juice or muffins was provided as advertised.

Reviewed on Nov 10, 2025

Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

17.6/10 Exceptional! (1,082 reviews)

Jan 7 - Jan 12

5 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Frontier Airlines • Coach
Price was $891, price is now $335 per person
$335
per person
found 1 day ago
The location is conveniently close to Universal, with a nearby 7-Eleven and several restaurants. The room is clean and pleasant, and parking is easily accessible.

Reviewed on Aug 6, 2025

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Casselberry packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Florida Hotel & Conference Center in the Florida Mall
3.5-star property

Florida Hotel & Conference Center in the Florida Mall

18.4/10 Exceptional! (2,220 reviews)

Jan 9 - Jan 12

3 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $894, price is now $578 per person
$578
per person
found 1 day ago
We love Florida Hotel, it is right inside the mall which made our stay enjoyable. The room is spacious and cozy and what really made us love the Hotel is the staff who are very attentive to us. Mr. Ted Kopsaftis was very helpful and he has a heart of gold for his unwaivering assistance with my return packages to amazon. I would have been miserable without his help. He went above and beyond helping me settle my problem with amazon. Thank you Florida Hotel for having an amazing staff.

Reviewed on Feb 4, 2025

Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

17.6/10 Exceptional! (1,082 reviews)

Jan 9 - Jan 12

3 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $885, price is now $625 per person
$625
per person
found 1 day ago
The location is conveniently close to Universal, with a nearby 7-Eleven and several restaurants. The room is clean and pleasant, and parking is easily accessible.

Reviewed on Aug 6, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays
4.0-star property

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9/10 Wonderful! (1,003 reviews)

Jan 9 - Jan 12

3 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,184, price is now $890 per person
$890
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.

Reviewed on Oct 7, 2024

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More About Flying To Casselberry from Chicago

Route Information for Flights from Chicago to Casselberry

Origin Airport IATA Code
CHI
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Casselberry

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.